6729-60-8

Usage

Uses

Used in Organic Synthesis:
Dichloro(tri-O-tolyl)bismuth is used as a catalyst for various organic reactions, facilitating the formation of carbon-carbon and carbon-heteroatom bonds. Its unique catalytic properties make it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, dichloro(tri-O-tolyl)bismuth is used as a catalyst for the synthesis of active pharmaceutical ingredients. Its ability to promote the formation of essential chemical bonds contributes to the development of new and improved drugs.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, dichloro(tri-O-tolyl)bismuth is employed as a catalyst for the synthesis of agrochemicals, such as pesticides and herbicides. Its catalytic properties aid in the production of more effective and environmentally friendly agrochemicals.
Used in Sustainable and Environmentally Friendly Chemical Processes:
Dichloro(tri-O-tolyl)bismuth is also used as a catalyst in the development of sustainable and environmentally friendly chemical processes. Its potential to minimize waste and reduce the environmental impact of chemical reactions makes it a promising compound for green chemistry applications.

InChI:InChI=1/3C7H7.Bi.2ClH/c3*1-7-5-3-2-4-6-7;;;/h3*2-5H,1H3;;2*1H/q;;;+2;;/p-2/rC21H21BiCl2/c1-16-10-4-7-13-19(16)22(23,24,20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3

Upstream product

• 10050-08-5 tri-o-tolylbismuth 
• 932-31-0 ortho-tolylmagnesium bromide 
• 95-46-5 2-methylphenyl bromide 
• 2028-34-4 o-toluene-diazonium chloride 
• 7647-01-0 hydrogenchloride 
• 233257-02-8 [(trifluoroacetyl)imino]tris-(2-methylphenyl)-λ(5)-bismuthane 

Downstream Products

• 36884-28-3 5-phenyl-1-pentanal 
• 343945-28-8 N-(2-methylphenyl)-2-piperidone 
• 874116-10-6 1-(2-methylphenyl)quinolin-2(1H)-one 
• 10050-08-5 tri-o-tolylbismuth 
• 313973-96-5 [(4-nitrobenzoyl)imino]tris(2-methylphenyl)-λ5-bismuthane 
• 313973-95-4 [(3,5-bis(trifluoromethyl)benzoyl)imino]tris(2-methylphenyl)-λ5-bismuthane 
• 233257-02-8 [(trifluoroacetyl)imino]tris-(2-methylphenyl)-λ(5)-bismuthane 
• 233257-03-9 [(trichloroacetyl)imino]tris(2-methylphenyl)-λ5-bismuthane 
• 417701-45-2 (mesylimino)tris(2-methylphenyl)-λ5-bismuthane 
• 417701-43-0 tris(2-methylphenyl)(tosylimino)-λ5-bismuthane 

Relevant academic research and scientific papers

Facile oxidation of alcohols to carbonyl compounds using a tris(2-methylphenyl)-bismuth dichloride-DBU binary system

High efficiency and chemoselectivity as well as the facile isolation of the carbonyl products by simple workup procedures characterize a new method of alcohol oxidation. A variety of primary and secondary alcohols are oxidized to aldehydes and ketones by the combined use of tris(2-methylphenyl)bismuth dichloride and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) under mild conditions [Eq. (1)].

Synthesis, structure, and reactions of (acylimino)triaryl-λ5-bismuthanes: First comparative study of the (acylimino)pnictorane series

The synthesis, structure, and reactions of (acylimino)triaryl-λ5-bismuthanes and a comparative study of the structure and reactivity of a series of (acylimino)pnictoranes are reported. Treatment of ortho-substituted triarylbismuth dichlorides 1 (Ar3BiCl2; Ar = 2-MeC6H4, 2-MeOC6H4, 2,4,6-Me3C6H2) with amides 2 (H2-NCOR; R = CF3, CCl3, 3,5-(CF3)2C6H3) in the presence of 2.2 equiv of KO-t-Bu in dichloromethane afforded (acylimino)triaryl-λ5-bismuthanes 3 (Ar3Bi=NCOR) in yields of 77-96%. The ortho-substituted aryl ligands and the electron-withdrawing N-substituents afford kinetic and thermodynamic stabilization, respectively, to the reactive Bi=N bond. The structures and properties of a series of (acylimino)pnictoranes (Ar3M=NCOR and H3M=NCOCF3; M = P, As, Sb, Bi) are compared by IR and 13C and 15N NMR, X-ray crystallography, and ab initio molecular orbital calculations. It was found that the contribution of the M+-N=C-O- canonical form becomes more prominent and the single-bond character of the M=N bond increases progressively as the pnictogen atom becomes heavier. The Bi=N bond of (acylimino)-λ5-bismuthanes 3 possesses a highly polarized single-bond character, probably due to the differences in orbital size and electronegativity between the bismuth and nitrogen atoms. Thermal decomposition of (aroylimino)triaryl-λ5-bismuthane 3f (o-Tol3Bi=NCOAr; Ar = 3,5-(CF3)2C6H3) produces a gel in dry conditions or aniline 12 (ArNH2) in slightly wet conditions with a good recovery of tris(2-methylphenyl)bismuthane (4a). It is likely that the aryl isocyanate 13 (ArNCO) is produced during the thermolysis via a concerted C → N migration of the Ar group with an elimination of the triarylbismuthonio group as bismuthane 4a. (Acylimino)triaryl-λ5-bismuthanes 3 oxidize 1,1,2,2-tetraphenylethanediol, benzenethiol, methanol, and ethanol to benzophenone, diphenyl disulfide, methyl formate, and acetaldehyde, respectively, in two different reaction pathways depending on the structure of the substrates. Compound 3d (o-Tol3Bi=NCOCCl3) transfers the nitrenoid moiety to triphenylphosphane, triphenylarsane, and tris(2-methylphenyl)stibane to give the corresponding (acylimino)pnictoranes (Ar3M=NCOCl3; M = P, As, Sb) and 4a, suggesting that 3d is thermodynamically much less stable than their lighter pnictogen counterparts. The copper-catalyzed decomposition of 3 (o-Tol3Bi=NCOR) afforded N-acyl-o-toluidines 18 (o-TolNHCOR) via a Bi → N migration of the tolyl group. The observed reactivities of (acylimino)triaryl-λ5-bismuthanes 3 demonstrate a good leaving ability of the bismuthonio group.

First synthesis, structure, and reactivity of (acylimino)triaryl-λ5-bismuthanes stabilized by ortho-substituted aryl ligands

The reactive Bi(V)=N bond in (acylimino)-triaryl-λ5-bismuthanes has been found to be stabilized effectively by ortho-substituted aryl ligands such as o-tolyl, o-anisyl, and mesityl groups. These imino-λ5-bismuthanes, in which the bismuth center possesses a distorted tetrahedral geometry, behave as a nitrene precursor as well as an oxidizing agent, depending on the substrates and conditions.